Reacción #2045002

Ecuación de reacción

Capsaicin

K2CO3

sodium iodide

disodium phosphate

methyl 6-bromohexanoate

→

12

Rendimiento 52.8%

6-{2-Methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenoxy}-hexanoic acid methyl ester

Rendimiento 52.8%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 24 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (15 ml) was added
4. 4
   FiltraciónCrude 12 was filtered
5. 5
   Otrodried
6. 6
   Otropurified by column chromatography on silica gel

Procedimiento

To a mixture of Capsaicin (2 g, 6.56 mmol), anhydrous K2CO3 (3 g, 22 mmol), sodium iodide (2 g, 13.3 mmol) and disodium phosphate (2 g, 14.2 mmol) in anhydrous acetone (50 ml) was added methyl 6-bromohexanoate (2 g, 9.6 mmol) and refluxed for 24 hours. Acetone was distilled off and water (15 ml) was added. Crude 12 was filtered, dried and purified by column chromatography on silica gel using benzene:ethyl acetate (9:1) to give pure 12 (1.5 g, 52.8%) as a pale white powder. The melting point was found to be 69.2-70.8° C.

Fuente